Damn Stihl, you got away easy on that one, only 2100 in damages. I will be very surprised if that is the final settlement.
One of my guys cracked a driveway a while back. It was a pos cracked up driveway from the beginning, though he should have been more careful. The insurance company ended up shelling out over ten grand.... I about shat myself. I had a quote from a reputable concrete company to replace the whole driveway for 2500, it was 3000 dollar removal so I was just gonna pay out of pocket. The homeowner insisted on making a claim.... now I know why.
There is no way you are gonna get him to pay up for that legally, unless he was a subcontactor on contract carrying his own liability insurance equal or greater to yours. If you don't fire him you could probably negotiate him paying the deductible in exchange for keeping his job, but that guy needs some supervision..... that #### is just dumb.